Oliver and Lilly's Infinite Playlist
by TheRightWrongs
Summary: A collection of songfics revolving around the pairing of Oliver Oken and Lilly Truscott
1. Love Story

**AN: This is the promised companion to "Jake and Miley's Infinite Playlist" It's following the same concept just a different pairing. My favorite pairing to be exact!! The song for this particular songfic is Kat McPhee's "Love Story" it's a great Loliver song!! Enjoy!!**

I guess you could say we were a typical love story. Oliver and Lilly, the best buds from preschool turned high school sweethearts.

_I think it was the summer time_

_When I laid eyes on you_

_I didn't even know you're name_

_Somehow we'd end up in the same room_

It started in the summer before preschool, not in preschool as it was previously believed. As I was only four years old at the time, my memory was a little fuzzy but leave it to my mother to remember something as odd as that day. I wanted to ride the seesaw but my brother didn't want to go on it with me. So instead of whining to my mom that he was being mean to me, I went on a quest to find a seesaw partner. My search didn't take me too far because once I began to walk away my mom freaked out and ran after me. I told her my seesaw dilemma; apparently I was a very diplomatic child that day because when she tried to force my brother to do it, I turned her down.

So as I gave up on the seesaw I headed over to the swings, but those were all occupied. I waited patiently for someone to leave to take my turn. Finally one of the boys got off the swing and ran away screaming that he wanted to go on the seesaw now. I followed him and asked if it was alright to ride with him. He looked reluctant to be seen with a girl but as there was a lack of available partners around he settled for me. As my mom tells me we rode the seesaw for a minute before we both got bored and ran off in different directions. I never even got his name that day but we eventually met up a few weeks after once school started. And the rest they say is history.

_Never crossed my mind_

_I never saw you like that _

_I should've listened to my best friend_

_She knew we'd be a perfect match_

We were inseparable after that. I guess that's when my tom boyishness came into effect. Then Miley came in the seventh grade. She once told me that Oliver and I made a cute couple, I laughed then set her straight. We were strictly platonic, I've never even thought about dating him, besides he wasn't my type; not that I had a type. The idea was completely ludicrous, but she never let it go; constantly reminding me about the crayon incident. Honestly though I didn't see what the big deal was, we were only four for goodness sake!

_I always made up some excuse_

_Saying' that you weren't my type_

_Didn't want to face the truth_

_Didn't want to cross that line_

_Till one day I saw you_

_Out of the corner of my eye_

_You were flirting with some girl_

_And inside I thought I would die_

Ok so you're probably wondering how we became a 'typical love story' right. Well it all began during the summer before junior year and just snowballed from there. Robbie was throwing a graduation party for Jackson; believe it or not he actually graduated. He invited a lot of people including many "babes" as Jackson referred to them. Of course Miley, Oliver and I were invited (his dad threatened him to) It was being held at the beach which meant many girls walking around in skimpy skirts and bikini tops. Of course Oliver being the hormonal sixteen years old he was began flirting up a storm. Most girls turned him down but there was this one redhead in particular who flirted back. Once I saw this, a horrible feeling churned in the pit of my stomach. I became sick at the sight of them I ended up walking away towards Miley's house. I couldn't understand my reaction until Miley talked to me.

She made me see that I liked Oliver as more than just a friend, after twenty minutes of protesting and denying it. She gave up and walked away to get a drink. I was on the Stewart's deck when I heard footsteps coming back a couple of minutes later. Thinking it was just Miley, I didn't bother to wipe the tears that had fallen. The footsteps stopped and I looked up into the concerned eyes of Oliver. That's when it hit me; I was in love with Oliver. This realization just caused me to burst into tears again. Oliver dragged me out of my chair and pulled me into a hug. He didn't even know what was wrong, but he knew that it had to be something major to make Lilly Truscott cry.

After a good five minutes of crying I broke down and told him everything; how I had been avoiding my feelings for so long, how I died a little inside when I say him with another girl, and how I was completely and totally in love with him.

_Can't believe its happening_

_When I least expect it_

_My prince under disguise_

_How you fooled me with those eyes_

_When I feel like letting go_

_In your arms is where I know_

He stared at me for a while before responding, usually I'm an impatient girl but after dumping all of that information on him I understood that he needed a little time to digest it all. After a good minute or two he told me what he felt. He told me about how he had also been avoiding the same feelings as me, how Lindsay (the redhead) was just using him to get Jackson jealous, and how he agreed to let her use him. I just sat there hoping that he would tell me that he loved me too, but it didn't come. Instead he scooped me up bridal style, (when did he get so strong?!) and kissed me. Silence followed this kiss until he broke it to say that he loved me too.

_It's a typical love story_

_We started out as friends_

_We met way back when_

_This is just a _

_Typical love story_

_The boy you never wanted_

_Just steals your heart_

_I never saw it coming' _

_Till I fell so hard_

We never did end up going back to the party. I recall Miley and a certain blonde action star coming to join us in our solitude. The four of us decided to forgo the rest of the party and just hang out. The rest of the summer went by quickly as it always does. School began and Oliver and I made it through the whole summer together. I can still clearly remember the shocked faces of Amber and Ashley, who had gone on vacation to Hawaii for the entire summer, when we walked into homeroom hand in hand. They were priceless. Almost as priceless as when they found out that Jake was coming back to public school; which was almost as priceless as when they found out that he was still dating Miley. Yeah junior year was quite memorable. Now I can only imagine what senior year had in store for me, yikes!

AN: What do you think? Please review!! If you have any ideas for songs then please tell me in a review!!


	2. Fall For You

**AN: Here is the second songfic of this series. I got two requests for songs and this is the first one. I dedicate "Fall For You" to TraceCyrusishottt. A special thanks to amandajbruce for giving me the push I needed to update this. The second request should be up by the end of the week. (fingers crossed!)**

**SONG: Fall For You  
ARTIST: Secondhand Serenade  
Because every perfect couple fights...**

"_Kelly Clarkson is so much better than her!" Lilly Truscott screamed at the mop-topped boy that was sitting across from her._

"_Carrie Underwood is the best, how can you say that?" Oliver Oken yelled back at his girlfriend._

"_What you guys fighting about now?" Miley Stewart asked her two friends._

"_Who the best American Idol is, it's definitely Kelly," Lilly answered sticking her tongue out at her boyfriend._

_Oliver just laughed at his girlfriend and mimicked her. Lilly then giggled and went in for a hug._

"_You guys are so weird," Miley said as she watched her two friends go from a heated argument to a loving embrace._

**(Oliver's POV)**_  
_We always get into fights but it was never anything serious. We'd fight and make up in a matter of minutes; it was just how we were. Lately though the fights have become more vicious and longer lasting. It's been a whole week since we've spoken last, and I miss her so much. Lilly was one of a kind and impossible to find.

**(Lilly's POV)**  
"Miley I miss him," I whined to my best friend.

I was over her house for the night just trying to forget the ridiculousness of my fight with Oliver.

"I know you do, and I'm sure he misses you too," she said trying to comfort me.

"But what if he doesn't? We've never gone this long without at least seeing each other," I cried.

"Lilly, Oliver loves you have nothing to worry about," Miley said as she patted my back trying to calm me down.

"God that fight was so stupid, I can't even remember what it was about!" I said as I buried my face into one of Miley's throw pillows and continued to cry myself dry.

**(3****rd**** Person POV)**  
Lilly's sobs quieted after a few moments. Silence filled the room as Miley sadly watched her best friend fall to pieces.

After a couple of minutes later, Miley's phone vibrated signaling a text. She grabbed it and read it quickly as Lilly lifted her head from the pillow.

"Who was it?" She asked curiously.

"Just Jake, he wants to know if we're still on for tonight," Miley answered.

"Oh I'm sorry, I didn't know, I'll just go now," Lilly said getting up to leave.

"No don't worry about it, I told him that we'd meet later. But now I feel like going out with my best friend,"

"Thanks but you don't have to do that for me," Lilly said shaking her head.

"Lilly, I know I don't have to but I want to. Come on let's go out for ice cream or something, my treat,"

Lilly looked at her friend an accepted the invitation.

The two girls grabbed their purses and headed downstairs. Miley locked the door behind her and left a spare key under the plant on her porch.

"What's that for?" Lilly asked.

"Oh Jackson left his keys at home this morning, I have a feeling he's going to need it if he plans on getting in the house legally when he comes home from work."

"Oh, right," Lilly said as she laughed out loud at her best friend's brother.

The girls walked down to the boardwalk, and sat down at the counter of Rico's. They ordered their sundaes from the employee behind the counter before turning around to gaze out at the beach.

"We should start heading back Lilly," Miley said.

"Oh yeah, let's go," Lilly said putting a smile on her face. The girls walked the mile back to Miley's beach house. "It looks like your dad isn't home anymore."

"Oh yeah, he's at a meeting with Hannah's record label. He must have just left," Miley said glancing at the time on her cell.

The girls walked up the driveway before Miley remembered something.

"Hey I just need to get something out of my car, go ahead here are the keys."

"Ok thanks," Lilly said as she walked up to the glass double doors.

What she saw when she opened them shocked her. There was a rose petal path that led to the deck out back.

"Um Miley, I don't think Jake got the message," She called out behind her.

Not a second after she said that did music start playing around her.

Secondhand Serenade's "Fall For You" filled her ears, as she walked in the house further.

_**The best thing about tonight is that we're not fighting  
Could it be that we have been this way before  
I know you don't think that I am trying  
I know you're wearing thin down to the core**_

"Lilly?" Oliver said as he walked into the house from the back entrance.

Tears threatened to spill from her eyes as her eyes landed on his sincere face.

_**But hold your breath  
Because tonight will be the night  
That I will fall for you  
Over again  
Don't make me change my mind  
Or I won't live to see another day  
I swear it's true  
Because a girl like you is impossible to find  
You're impossible to find**_

"Oliver?" Lilly answered uncertainly.

Oliver walked up to her and engulfed her in a hug before taking her by the hand and leading her outside along the rose petal path. She followed him silently, the tears flowing freely by then.

_**This is not what I intended  
I always swore to you I'd never fall apart  
You always thought that I was stronger  
I may have failed but I have loved you from the start**_

"Lilly I'm so sorry; I didn't mean what I said to you; I always have and always will love you," Oliver said taking her hands in his.

Lilly continued to stare at him, her tears beginning to subside. Oliver reached over with his left hand to push her bangs away from her face. He placed the stray blonde hair behind her right ear and proceeded to wipe the left over tears from her flushed cheeks.

Lilly closed her eyes, cherishing his touch. She opened her eyes to see Oliver gazing at her with a hopeful smile. She smiled back as she closed the minimal space between them and mimicked his earlier hug.

"I'm sorry too," she whispered in his ear, causing chills to go down his spine.

_**So breathe in so deep  
Breathe me in  
I'm yours to keep  
And hold on to your words  
Cause talk is cheap  
And remember me tonight  
When you're asleep**_

They gazed at each other in silence for a few moments. In the middle of this silence, Lilly's phone started to play the customized ringtone for Miley. She was about to ignore the call when Oliver snatched the phone out of her hand and answered it instead.

"Thanks Miley, but Lilly is quite busy now, she'll have to call you back later,"

"Give me the phone" Lilly laughed grabbing the phone back.

"Hey Miley, thank you; have fun with Jake tonight," Lilly said jokingly as she hung up the phone before her friend had time to respond. Laughing at her own joke she looked up at Oliver. He had taken her face gently into his hands and lowered his lips onto her quickly. Lilly immediately responded by placing her own hands on top of his bringing them down near her waist and then skillfully wrapping her arms around his neck, pulling him closer until there was no space between them.

**_Because tonight will be the night  
That I will fall for you  
Over again  
Don't make me change my mind  
Or I won't live to see another day  
I swear it's true  
Because a girl like you is impossible to find_**

_Tonight will be the night  
That I will fall for you  
Over again  
Don't make me change my mind  
Or I won't live to see another day  
I swear it's true  
Because a girl like you is impossible to find  
You're impossible to find_

They hadn't known how long they had stood there like that, and didn't care either until they were interrupted by the ever immature Jackson Stewart.

"Just get a room already!" He yelled at the pair as he ran up the stairs to his own room.

They gladly listened to him and ran from the Stewart household hand in hand.

**AN: Gah! That ending was unbelievably corny and fluffy and every other synonym of those words. Oh well, I liked it! Please review and request more songs!**

**Poll Question: Do you think I should expand "Love Story"? Put the answer in a review!**


End file.
